Anacardic AcidShown to potently inhibit HAT-dependent transcription and SUMOylation

Anacardic Acid (CAS 16611-84-0)

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Sinónimo: 6-Pentadecylsalicylic acid
Solicitud: Shown to potently inhibit HAT-dependent transcription and SUMOylation
Número de CAS: 16611-84-0
Pureza: ≥95%
Peso Molecular: 348.52
Fórmula Molecular: C22H36O3
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Anacardic Acid is a pentadecane aliphatic chain containing hydroxylcarboxylic acid. The acid is an effective inhibitor of the activities of p300, p300/CBP associated factor histone acetyltransferase, prostaglandin synthase (PTGS2 or Cox-2), tyrosinase, urease-α and -β, lipoxygenase (LO), and xanthine oxidase. Additionally, it has been shown to potently inhibit HAT-dependent transcription and SUMOylation, as well as decrease expression of NF-κB regulated gene products at high concentrations. Research suggests that anacardic acid is a potent activator of ARK-1 (Aurora kinase A) mediated phosphorylation of histone H3 while leaving ARK-2 unaffected in vitro. Anacardic acid has demonstrated bactericidal activity against methicillin-resistant Staphylococcus aureus (MRSA).


References

1. Muroi, H., et al., 1996. Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus. The Journal of applied bacteriology. 80(4): 387-94. PMID: 8849640
2. Paramashivappa, R., et al., 2002. Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition. Journal of agricultural and food chemistry. 50(26): 7709-13. PMID: 12475293
3. Balasubramanyam, Karanam., et al., 2003. Small molecule modulators of histone acetyltransferase p300. The Journal of biological chemistry. 278(21): 19134-40. PMID: 12624111
4. Kishore, A Hari., et al., 2008. Specific small-molecule activator of Aurora kinase A induces autophosphorylation in a cell-free system. Journal of medicinal chemistry. 51(4): 792-7. PMID: 18215015
5. Sung, Bokyung., et al., 2008. Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-kappaB-regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-kappaBalpha kinase, leading to potentiation of apoptosis. Blood. 111(10): 4880-91. PMID: 18349320
6. Fukuda, Isao., et al., 2009. Ginkgolic acid inhibits protein SUMOylation by blocking formation of the E1-SUMO intermediate. Chemistry & biology. 16(2): 133-40. PMID: 19246003

Uso :
Stock solutions are stable for up to 3 months when stored at -20°C.
Estado de Materia :
solid
Forma Derivada :
Synthetic
Solubilidad :
Soluble in ether, petroleum ether, DMSO (≥20 mg/mL), DMF (~10 mg/mL), ethanol (~10 mg/mL), a1:1 solution of ethanol:PBS(pH7.2) (~0.5 mg/ml), methanol, dichloromethane, and ethyl acetate.
ALMACENAMIENTO :
Store at 4° C
Punto de Fusión :
33.9-37.2° C
Punto de ebullición :
474.82° C at 760 mmHg
Densidad :
1.00 g/cm3
Indice de Refracción :
n20D 1.52
IC50 :
PCAF: IC50 = 8.5 µM; HAT: IC50 = 5 µM; HIV-1(RF): IC50 = 49.35 µM (CEM-SS); HIV-1(RF): EC5050 = >61.69 µM (CEM-SS); Protein SUMO and modification: IC50 = 2.2 µM
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
WGK Alemania :
1
PubChem CID :
167551
Indice de Merck :
14: 621
Número MDL :
MFCD07368254
SMILES :
CCCCCCCCCCCCCCCC1=C(C(=CC=C1)O)C(=O)O

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Anacardic Acid  Menciones del Producto

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PMID: # 30958996  2019. Chem. Biol. Interact. 306: 54-61.

PMID: # 31272829  Fang, MY.|Markmiller, S.|Vu, AQ.|Javaherian, A.|Dowdle, WE.|Jolivet, P.|Bushway, PJ.|Castello, NA.|Baral, A.|Chan, MY.|Linsley, JW.|Linsley, D.|Mercola, M.|Finkbeiner, S.|Lecuyer, E.|Lewcock, JW.|Yeo, GW.| et al. 2019. Neuron.

PMID: # 25338966  Kang, MA. et al. 2015. International journal of oncology. 46: 342-50.

PMID: # 22102278  Masola, V. et al. 2012. J. Biol. Chem. 287: 1478-88.

PMID: # 22562121  Jain, S. et al. 2012. Breast cancer research and treatment. 135: 103-14.

PMID: # 21551354  Czakai, K. et al. 2011. Toxicological sciences : an official journal of the Society of Toxicology. 122: 317-29.

Citaciones 1 a 6 de un total de 6
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